JP2017501197A - 5−フルオロ−4−イミノ−3−(アルキル/置換アルキル)−1−(アリールスルホニル)−3,4−ジヒドロピリミジン−2(1h)−オンおよびそれらの調製方法 - Google Patents
5−フルオロ−4−イミノ−3−(アルキル/置換アルキル)−1−(アリールスルホニル)−3,4−ジヒドロピリミジン−2(1h)−オンおよびそれらの調製方法 Download PDFInfo
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- 0 *c(cc1)ccc1S(N(C=C(C(N1*)=N)F)C1=O)(=O)=O Chemical compound *c(cc1)ccc1S(N(C=C(C(N1*)=N)F)C1=O)(=O)=O 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
- C07D333/10—Thiophene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Abstract
Description
本出願は、各開示が参照により本明細書に特に組み込まれる2013年12月31日出願の米国特許仮出願第61/922,572号および第61/922,582号の利益を主張する。
本明細書において、5−フルオロ−4−イミノ−3−(アルキル/置換アルキル)−1−(アリールスルホニル)−3,4−ジヒドロピリミジン−2(1H)−オンおよびそれらの調製方法が提供される。
米国特許出願第13/090,616号、米国特許公開第2011/0263627号には、とりわけあるN3置換−N1−スルホニル−5−フルオロピリミジノン化合物およびそれらの防カビ剤としての使用が記載されている。この出願の開示は、参照により本明細書に特に組み込まれる。この特許には、N3置換−N1−スルホニル−5−フルオロピリミジノン化合物を生成させる種々の経路が記載されている。N3置換−N1−スルホニル−5−フルオロピリミジノン防カビ剤および関連化合物を調製、単離、および精製するためのより直接的および効率的な方法を、例えば、試薬および/または化学的中間体の使用ならびに改善された時間およびコスト効率を提供する単離および精製技法により提供することは有益であろう。
の化合物を調製するための方法であって、式IIの化合物を、塩基、例えば、アルカリ炭酸塩、例えば、炭酸ナトリウム、炭酸カリウム、炭酸セシウムおよび炭酸リチウム(それぞれ、Na2CO3、K2CO3、Cs2CO3およびLi2CO3)またはアルカリアルコキシド、例えば、カリウムtert−ブトキシド(KOtBu)およびアルキル化剤、例えば、式R2−X(式中、R2は前に定義されたものであり、Xはハロゲン、例えば、ヨウ素、臭素、および塩素である)のハロゲン化アルキルと、極性溶媒、例えば、N,N−ジメチルホルムアミド(DMF)、ジメチルスルホキシド(DMSO)、ジメチルアセトアミド(DMA)、N−メチルピロリドン(NMP)、アセトニトリル(CH3CN)などの中で、約0.1モル/L(molar)(M)から約3Mの濃度で接触させることを含む、方法が本明細書中で提供される。幾つかの実施形態では、式IIの化合物と塩基とのモル比は、約3:1から約1:1であり、式IIの化合物とアルキル化剤とのモル比は、約1:1から約3:1である。他の実施形態では、式IIの化合物と塩基とのモル比および式IIの化合物とアルキル化剤とのモル比は、それぞれ約2:1および約1:3が使用される。幾つかの実施形態において、反応は−78℃と90℃の間の温度で実施され、他の実施形態では、反応は22℃と60℃の間で実施される。
の化合物を形成させるステップとを含み、化合物Iとビス−N,O−トリメチルシリルアセトアミド(BSA)とのモル比は、1:1.1であり、接触させるステップは約22℃から約70℃で実施する。
実施例1〜2に示した5−フルオロ−4−イミノ−3−(アルキル/置換アルキル)−1−(アリールスルホニル)−3,4−ジヒドロ−ピリミジン−2(1H)−オン。
Claims (17)
- 前記接触させるステップが22℃と60℃の間で実施される、請求項1に記載の方法。
- 前記接触させるステップが、DMF、DMSO、DMA、NMP、およびCH3CNからなる群から選択される溶媒をさらに含む、請求項1に記載の方法。
- 前記アルカリアルコキシドが、KOtBu、CH3ONa、CH3CH2ONa、CH3CH2OLi、CH3OLi、CH3CH2OKおよびCH3CH2ONaからなる群から選択される、請求項1に記載の方法。
- 前記アルキル化剤が、ハロゲン化アルキルおよびハロゲン化ベンジルからなる群から選択される、請求項1に記載の方法。
- 前記ハロゲン化アルキルおよびハロゲン化ベンジルが、ヨウ化メチル、ヨウ化エチル、および臭化ベンジルからなる群から選択される、請求項5に記載の方法。
- 前記アルカリアルコキシドがKOtBuであり、前記溶媒がDMFである、請求項3、4、5、または6に記載の方法。
- 式IIの化合物とアルカリアルコキシドとのモル比が約3:1から約1:1であり、式IIの化合物とアルキル化剤とのモル比が約1:1から約3:1である、請求項2、3、4、5、6、または7に記載の方法。
- 式IIの化合物とアルカリアルコキシドとのモル比が約2:1であり、式IIの化合物とアルキル化剤とのモル比が約1:3である、請求項8に記載の方法。
- 反応の完了した混合物をCH3CNおよび2.5%Na2S2O3水溶液で希釈するステップをさらに含む、請求項9に記載の方法。
- DMFとCH3CNとの比が約1:1から約3:1であり、DMFと2.5%Na2S2O3水溶液との比が約1:2から約2:1である、請求項10に記載の方法。
- DMFとCH3CNとの比が約2:1であり、DMFと2.5%Na2S2O3水溶液との比が約1:1である、請求項11に記載の方法。
- 前記接触させるステップが、化合物IをCH3CNと接触させることをさらに含む、請求項13に記載の方法。
- 前記ビス−N,O−トリメチルシリルアセトアミドで処理された反応混合物をアリールスルホニルクロリドと接触させるステップをさらに含む、請求項14に記載の方法。
- 式Iの化合物とアリールスルホニルクロリドとのモル比が約1:2から約2:1である、請求項15に記載の方法。
- 式Iの化合物とアリールスルホニルクロリドとのモル比が約1:1.1である、請求項16に記載の方法。
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US201361922572P | 2013-12-31 | 2013-12-31 | |
US201361922582P | 2013-12-31 | 2013-12-31 | |
US61/922,572 | 2013-12-31 | ||
US61/922,582 | 2013-12-31 | ||
PCT/US2014/072569 WO2015103144A1 (en) | 2013-12-31 | 2014-12-29 | 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation |
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AP (1) | AP2016009342A0 (ja) |
AU (2) | AU2014373959B2 (ja) |
BR (2) | BR102014033037B1 (ja) |
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